Process for the manufacture of the antibiotic 7-(D-.alpha.-amino

Details Process for the manufacture of the antibiotic 7-(D-.alpha.-amino Process for the manufacture of the antibiotic 7-(D-.alpha.-amino

1997-07-09

1999-06-01

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49912, C07C22936

Patent

active

059089296

ABSTRACT:
A process for the manufacture of the antibiotic 7-(D-.alpha.-amino-.alpha.-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid (cephalexin) and pharmaceutically acceptable salts thereof. It consists of reacting an enamine protected potassium salt of D-(-)-.alpha.-phenyl glycine (Dane salt) with an acid chloride in a twin solvent mixture in the presence of a pyridine derived twin catalytic mixture at -20 to -65.degree. C. The resulting mixed anhydride is condensed with an alkyl guanidinium salt solution of 7-amino desacetoxy cephalosporanic acid (7-ADCA) at -10.degree. C. to -65.degree. C. followed by hydrolytic cleavage of the enamine derivative of the resulting compound with an aqueous mineral acid and precipitation of the antibiotic in the presence of an alcohol as co-solvent. If desired the cephalexin is converted into its pharmaceutically acceptable salts in a known manner.

REFERENCES:
patent: 3507861 (1970-04-01), Morin et al.
patent: 3518260 (1970-06-01), Spencer et al.
patent: 3634416 (1972-01-01), Schofield
patent: 3671449 (1972-06-01), Jackson
patent: 3676437 (1972-07-01), Siddons
patent: 3694437 (1972-09-01), Jackson
patent: 3864340 (1975-02-01), Ishimaru et al.
patent: 4299955 (1981-11-01), Falciani et al.

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